Propylamine → HCID 67834777, compound

HRID 330154Notes

Reaction equation

HRID 330154 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=O)[CH:8]=2)[CH:3]=[CH:2]1.Cl.C[N:17](C)[CH2:18][CH2:19][CH2:20]N=C=NCC.C(N)CC.N=C=N>CN(C)C1C=CN=CC=1.C(Cl)Cl.CN(C)C=O>[CH2:18]([NH:17][C:12](=[O:14])/[CH:11]=[CH:10]/[C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1)[CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 7852Propylamine2×HCID 160435CarbodiimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14882675HCID 14882675, compound

Product 1

HCID 67834777HCID 67834777, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of E-indole-6-acrylic acid (0.96 g), 4-dimethylaminopyridine (0.635 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.96 g) was dissolved in methylene chloride (50 ml) and N,N-dimethylformamide (60 ml) and stirred for 1 hour. Propylamine (0.591 g) was added and stirring continued for 18 hr. Further quantities of 4-dimethylaminopyridine (0.635 g), the carbodiimide (0.96 g) and propylamine (0.591 g) were added; and the mixture stirred for a further 30 hr. The solvents were evaporated; the residue partitioned between ethyl acetate and 1M hydrochloric acid; and the organic phase washed with water and brine; dried (MgSO4); and evaporated. The residue was purified by flash chromatography, eluting with 1:10 methanol:chloroform, to give E-N-propylindole-6-acrylamide (0.7 g, 60%) as an off-white solid; partial NMR (250 MHz, DMSO-d6): 0.89(t, 3H, CH2CH2CH3, 1.48(m, 2H, CH2CH2CH3), 3.15(m, 2H, CH2CH2CH3); 6.44(d, J=2.8 Hz H3 -indole), 6.55(d, J=15.7 Hz, 1H, olefinic H), 8.00(br t, 1H, NHCO), 11.28(br s, 1H, H1 -indole).

Workup

  1. stirringand the mixture stirred for a further 30 hr
  2. customThe solvents were evaporated
  3. customthe residue partitioned between ethyl acetate and 1M hydrochloric acid
  4. washand the organic phase washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customand evaporated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 1:10 methanol

Sources & evidence

ORD record
ord-31ad08c8dfea4704b9abe391ed70401e
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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